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Synthesis and Characterization of Pyrrolo[3,4-d]Pyridazine-5,7-Dione-Based Conjugated Polymers for Organic Thin-Film Transistors

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Two new conjugated polymers, poly{6-(2-dodecylhexadecyl)-1,4-di(thiophen-2-yl)-5H-pyrrolo[3,4-d]pyridazine-5,7(6H)-dione-alt-2,2′-bithiophene} (PPz-BT) and poly{6-(2-dodecylhexadecyl)-1,4-di(thiophen-2-yl)-5H-pyrrolo[3,4-d]pyridazine-5,7(6H)-dione-alt-3,3′-dimethoxy-2,2’-bithiophene} (PPz-MeOBT), which contain methoxy-substituted and unsubstituted bithiophene units, respectively, were designed and synthesized. Experimental results revealed that the introduction of methoxy groups increases the highest occupied molecular orbital and lowest unoccupied molecular orbital energy levels of the polymer because of the electron donating ability of the methoxy group and improves the planarity of the conjugated polymer backbone. However, the two-dimensional grazing incidence X-ray diffraction pattern of the PPz-MeOBT thin film reveals a bimodal structure, whereas the PPz-BT thin film shows a predominant edge-on orientation. As confirmed by X-ray analysis, after thermal annealing at 280 °C, top-gate/bottom-contact organic thin-film transistors fabricated with PPz-BT show a higher field-effect mobility (2 × 10−3 cm2V−1s−1) compared to those fabricated with PPz-MeOBT (4 × 10−4 cm2V−1s−1).
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Keywords: Conjugated Polymer; Organic Thin-Film Transistor; Pyrrolopyridazine

Document Type: Research Article

Affiliations: 1: Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Busan 609-735, Republic of Korea 2: Department of Energy and Materials Engineering, Dongguk University 30 Pildong-ro, 1 gil, Jung-gu, Seoul 04620, Republic of Korea 3: Division of Convergence Chemistry, Research Center for Green Fine Chemicals, Korea Research Institute of Chemical Technology, Ulsan 44412, Republic of Korea

Publication date: October 1, 2017

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  • Journal for Nanoscience and Nanotechnology (JNN) is an international and multidisciplinary peer-reviewed journal with a wide-ranging coverage, consolidating research activities in all areas of nanoscience and nanotechnology into a single and unique reference source. JNN is the first cross-disciplinary journal to publish original full research articles, rapid communications of important new scientific and technological findings, timely state-of-the-art reviews with author's photo and short biography, and current research news encompassing the fundamental and applied research in all disciplines of science, engineering and medicine.
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